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I know folks have had mixed experiences with iTunes Match over the years, but I'm wondering about the current state of the platform. I have more than 30,000 songs in my iTunes library now, many of which were imported from CD at relatively low quality in the early days of iTunes as a product, as well as quite a few DRM-encoded 128 kbps songs from the early days of the store. I'm thinking of turning on iTunes Match as a way to upgrade as many of these songs as possible to better quality, DRM-free versions.
Does anyone have recent experience with a similar task? Of course, I'll make an archival backup of my current library before I start mucking around and deleting/downloading things, I know that not everything that once was available in the iTunes Store is still available, and I know that not all songs can be "matched," but are there any specific glitches and gotchas I should be looking for?

iTunes Match is very sketchy and has been for years. That said, I still use and pay for it. It used to work perfectly. Every CD I ripped with iTunes was matched. Then some years ago something changed and some tracks would be matched, others uploaded (not matched). Sometimes almost all would be uploaded and only a few tracks matched. And these were always with CDs that were actually in the iTunes store. It continues that way, although more now seem to be matched. But it has never equaled the perfection of the early days.

Good summary. I have used Match since it became available, primarily to upgrade lower-quality MP3 and AAC tracks to 256 Kbps. I also have multiple Apple devices, and it was a way to synchronize their libraries.

My question is, now that I have signed up for Apple Music/iCloud Music, am I really gaining anything from keeping Match? I still have multiple devices (all of which can access Apple Music), but I certainly don't need to upgrade bit rates anymore.

Good summary. I have used Match since it became available, primarily to upgrade lower-quality MP3 and AAC tracks to 256 Kbps. I also have multiple Apple devices, and it was a way to synchronize their libraries. My question is, now that I have signed up for Apple Music/iCloud Music, am I really gaining anything from keeping Match? I still have multiple devices (all of which can access Apple Music), but I certainly don't need to upgrade bit rates anymore.

• Apple Music is a subscription - you don't, and never will, own the music. When you stop paying, you will lose access to all the music you don't already own.​

If you're happy to pay Apple for the rest of your music listening life, you probably don't need Match.

In addition, Apple Music only gives you access to what's in Apple's music library - for most people, that's fine but, for example, in my own personal (but probably unusual) case, around 30% of the music I own isn't in the Apple Music library. When you consider my collection is currently 75,000+ tracks and 7,500+ CDs (not all ripped yet), that's a lot of music that Apple doesn't have and that Apple Music will never give me access to.

Graham, thanks for the detailed reply and the tips! Your article is one of the resources I've been consulting as I've been thinking about using iTunes Match. I agree with the comment about mismatched tracks and mismatched artwork. Even in the basic iTunes app, the accuracy of data delivered by the "Get Album Artwork" and "Get Track Names" can be shockingly poor. I wish those commands could be used selectively, i.e. for one or a few songs, rather than for an entire library. After some hard lessons, I now treat those commands as being downright harmful. For example, I buy a lot of my CDs through Amazon, which imports songs and artwork accurately into iTunes if the CD purchase includes Amazon's "Autorip" feature. After choosing "Get Album Artwork" in iTunes, quite a few correct album images from Amazon were replaced with wildly inaccurate images. Fortunately, I did have a backup of my library handy.

Thanks for the support. :-) I don't use Apple's "Get Album Artwork" and "Get Track Names", either, as I had exactly the same problems with mismatches and I'm very fussy with the cataloguing of my music.

It's a lot of hard work to manually keep my iTunes metadata and artwork correct, but I'm a bit OCD (Obsessive-Compulsive Disorder) with my library. I manually remove and add artwork as required, and I manually edit the metadata - it takes time, but, in my case, it is worth it. Documenting the steps I took meant I could keep the consistency across the library, and it helped me write my tagging articles on MacStrategy. As for artwork, I prefer hi-quality artwork, as it looks amazing when playing back via an Apple TV on a 1080p HD television. This requires sourcing at least 1000x1000-pixel artwork, which is not easy. Fortunately, I have found a way to grab hi-res artwork from Apple's iTunes online library, which I can't post here, as I don't want Apple to shut that route down. There's also my own... web site, The World Wide Release DataBase (WWRDB).

The Amazon Auto-rip service is quite good, but do note that you are only getting lossy MP3s, even if you buy a CD - these are lower quality than the CD itself.

With the advent of cheap, large-volume storage, I'm now slowly (re-)ripping my music to Apple Lossless (ALAC), and the quality is quite a lot different/better than MP3/AAC. Obviously, with a collection of 7500+ CDs, it's taking a while. ;-)

For help with metadata editing, I highly recommend Doug's Scripts For iTunes and, in the case of re-ripping, this process has been working really well for me:

Download and install Doug's Copy Tag Info Tracks to Tracks script, if you don't already have it (donate to/make a purchase from Doug, of course, if you haven't already).

In your iTunes library. select all the older, lower quality tracks in the whole album.

Get Info and change the metadata/tags for Grouping to include something that won't be used anywhere else e.g. "TODELETE" and append " OLD" to the album field.

Create a Smart Playlist to "Match Music" with the Grouping tag/field "Contains" to what you set in the previous step, e.g. "TODELETE", and tick "Live updating".

Re-rip the CD to ALAC/(re)import the original hi-res files (this won't flag up as duplicate/replace the older files, as you added OLD to the original files in step 3).

You now have an "OLD" set of files with your original/correct hard-worked metadata/tags/artwork plus a new set of files with incorrect/poor quality CDDB data and no artwork.

You will now have both the old and new files with identical tagging except the Grouping field - so now you can go to the "TODELETE" Grouping Smart Playlist you created in step 4, which will only show the old files, :-) select all the tracks and right/Control-click on them and select "Delete from Library" from the contextual menu - at the prompt, click to move the files to the Trash.

You are now left with only the new hi-resolution/re-ripped files in your library but with all your metadata/artwork hard work intact - all you have to do now is edit the new files to remove the appended " OLD" from the end of the Album field.

One final note: if you have original files in FLAC (or other lossless formats), you can use the excellent (donationware) X Lossless Decoder (XLD) to convert these to Apple's ALAC, ready to import into iTunes.

• Apple Music is a subscription - you don't, and never will, own the music. When you stop paying, you will lose access to all the music you don't already own.​

... In addition, Apple Music only gives you access to what's in Apple's music library - for most people, that's fine but, for example, in my own personal (but probably unusual) case, around 30% of the music I own isn't in the Apple Music library.

That's a great point, especially because songs available through the iTunes Store and through Apple Music (including otherwise unique songs or performances) can be removed from the Store/Music platforms without notice.

For example, I'm glad that I downloaded and kept copies of several "iTunes Originals" albums that I had purchased, as they no longer are available. Many of the Originals albums included truly interesting live performances and commentary by artists, and their disappearance is a real loss for fans.

That's a great point, especially because songs available through the iTunes Store and through Apple Music (including otherwise unique songs or performances) can be removed from the Store/Music platforms without notice. For example, I'm glad that I downloaded and kept copies of several "iTunes Originals" albums that I had purchased, as they no longer are available. Many of the Originals albums included truly interesting live performances and commentary by artists, and their disappearance is a real loss for fans.

It’s been a long time since I did this, but I experienced that if all the metadata for the CD matches that of the lossy tracks you previously ripped, iTunes offers to replace the files with new, freshly ripped files using the import settings currently in place.

I did this years ago for hundreds of CDs I ripped before I took iTunes seriously enough to rely on it. This technique maintains the playcount, last played, album cover art, and other metadata previously collected. It’s also an opportunity to review and correct the title and artist data.

... Hmmm, thinking about it again, I may be wrong about the artwork being retained.

As for artwork, I prefer hi-quality artwork, as it looks amazing when playing back via an Apple TV on a 1080p HD television. This requires sourcing at least 1000x1000-pixel artwork, which is not easy. Fortunately, I have found a way to grab hi-res artwork from Apple's iTunes online library, which I can't post here, as I don't want Apple to shut that route down.

Funnily enough, after having just stated this on MacInTouch, Apple, today, added a user enabled download artwork link to their official "Link Maker" web site:
https://linkmaker.itunes.apple.com/gb/?at=11l7jb

Select Media Type > Music and then enter your search terms. Click on the song/album artwork you want and the "Download Artwork" link is at the bottom :-)

Full disclosure: the "11l7jb" part of the link above is my iTunes affiliate ID - it doesn't affect your ability to use the Link Maker/download artwork, and it is always appreciated if you use before purchasing on iTunes, as it all helps fund MacStrategy.

Funnily enough, after having just stated this on MacInTouch, Apple, today, added a user enabled download artwork link to their official "Link Maker" web site:
https://linkmaker.itunes.apple.com/gb/?at=11l7jb
Select Media Type > Music and then enter your search terms. Click on the song/album artwork you want and the "Download Artwork" link is at the bottom :-)

It’s been a long time since I did this, but I experienced that if all the metadata for the CD matches that of the lossy tracks you previously ripped, iTunes offers to replace the files with new, freshly ripped files using the import settings currently in place.

I confirm that this is how iTunes has worked and currently works - it transfers tags and art. When you put in the CD, it asks you if you’d like to replace existing tracks.

I’m not 100% clear on how it handles files; it sometimes trashes existing files for music being replaced and sometimes doesn’t. My observation is that it trashes files it had created but leaves ones it didn’t.

The "Music" option is there for me - it did used to be listed as "iTunes Music", but that changed a few months ago. Perhaps when you access the Link Maker you're getting directed to a different server. Anyway, you're right, the artwork download link has disappeared - it was definitely there yesterday, because I was using it!

Mojave 10.14.4 seems to have, again, killed iTunes 12.6.5.3. It would not launch with some message about the version being incompatible.

Presuming that a new iTunes was installed I again tried the trick of moving the iPodUpdater.framework from the macOS 12.6.5 version to the new iTunes contents. But it looked like the framework file was still there, so maybe iTunes was not updated. I then tried this suggestion on a Macrumors forum, which involved replacing the info.plist file in iTunes 12.6.5 with the one from the new iTunes. I was then able to launch iTunes 12.6.5 and update apps in my Library.

However, backing up my iPhone failed every time, and iTunes showed no previous backups (they were still there in the Finder). So I replaced the info.plist file with the one iTunes 12.6.5 was using before the update, and then I was able to backup my iPhone as normal (and previous updates where showing in Preferences).

Strangely, iTunes 12.6.5 has a generic app icon in the Finder and has the "no symbol" (circle with diagonal line) in the Dock and in the app switcher. Maybe the iTunes 12.6.5 line is not quite dead, but it is looking grim.

I get annoyed every time I'm in iTunes and accidentally click on "Browse," "For You," or "Radio," all of which take me to Apple Music, a product I have zero intention of ever using. I assume that Apple's eventual Marzipan-flavored iTunes replacement will make this sort of pushy behavior even worse.

Thanks a lot for that tip. It ended up leading me to a more complete solution.

Your tip removed the "Browse" and "For You" buttons, but I was surprised that the Apple "Radio" button remained, and I wanted to get rid of that, too.

I started to ruminate about why Apple "Radio" somehow might not count as an "Apple Music Feature," especially given the fact that clicking on the Apple Radio button displays an "Apple Music" splash screen.

I decided to poke around the iTunes Preferences a little more, and I came across a separate checkbox on the "Restrictions" panel to disable "Apple Music." After checking that box, "Radio" finally disappeared from the iTunes navigation bar. Interestingly, in another example of hide-and-seek interface fashions, this also caused the "Show Apple Music Features" option to disappear from the "General" preferences panel.

Another potential source of confusion: the "Restrictions" panel also includes an option to disable "Internet Radio," which is a completely independent function from "Apple Radio." What a mess.

(At the risk of starting another rant, "Internet Radio" is a function I like very much and use quite a lot. When Apple launched Apple "Radio," it moved "Internet Radio" to a much less prominent place in iTunes, and it took me a little while to find it. At first, I thought Apple simply got rid of it entirely. I suppose I should count my blessings that Apple didn't kill it yet, though I fully expect that it won't survive the move to Marzipan apps.)

(At the risk of starting another rant, "Internet Radio" is a function I like very much and use quite a lot. When Apple launched Apple "Radio," it moved "Internet Radio" to a much less prominent place in iTunes, and it took me a little while to find it. At first, I thought Apple simply got rid of it entirely. I suppose I should count my blessings that Apple didn't kill it yet, though I fully expect that it won't survive the move to Marzipan apps.)

Internet Radio is the only reason I ever had to use iTunes. For numerous reasons, I gave up on iTunes about 3-4 years ago. I don't now nor have I ever needed an application to organize my files and media for me. I greatly prefer to do it my own way.

I now use the cross platform app VLC for Internet Radio and it works fine. I had to jump through a few hoops initially, but it's been great ever since.

I'm still using iTunes 12.6.5.3 (on Sierra), the last version that allows one to manage apps on their iDevices. Does anyone know if the iTunes Device Support Update interferes with that version of iTunes?

I'm still using iTunes 12.6.5.3 (on Sierra), the last version that allows one to manage apps on their iDevices. Does anyone know if the iTunes Device Support Update interferes with that version of iTunes?

I'm still using iTunes 12.6.5.3 (on Sierra), the last version that allows one to manage apps on their iDevices. Does anyone know if the iTunes Device Support Update interferes with that version of iTunes?

I have experienced no apparent interference with iTunes 12.6.5.3. That said, my use so far has been limited.

I've only done one iPhone sync/backup (and that just a moment ago). The update description says, "ensures proper updating and restoring for iOS devices…." I have neither updated nor attempted a restore.

The Apps section for my attached phone looks normal, but I haven't tried to install or remove an app. I was able to move an app icon on one screen.

I have been able to move songs to a phone. I was able to move two files to an app's File Sharing space (Apps > File Sharing > Apps > some app).

The iOS 12.3 upgrade did not go smoothly on my iPad Air (3rd Generation). I'm using iTunes 12.6.5.3 on macOS 10.13.6 High Sierra, and there is no iTunes Device Support Update offered. I attempted to update while connected via USB to iTunes.

First it said there was an error updating, and the dialog button led to

Restarting the iPad did not help. The next step, according to the linked website, was to do a factory reset, but I tried just telling iTunes to re-download and install the update.

That led to a screen I've never seen before: Press Home to Recover, and then an undocumented "Attempting Data Recovery" screen that took a very long time. While I waited, I read all the web articles that either a) said that they were stuck in an attempting data recovery loop with no escape, or b) tried to sell 3rd-party software to fix it.

Eventually the Data Recovery ended, and it restarted in iOS 12.3 with no data loss.

I wonder if the local (wireless) updates are more reliable than doing the full iTunes connected update? I would have thought not.

One last thought: All of Apple's support pages first say that you should upgrade to the latest version of iTunes. If it really is an issue using iTunes 12.6 to update, that presents a dilemma, since only iTunes 12.6 can completely restore an iDevice if something drastic goes wrong with the update.

As a follow-up to my earlier query, I installed the iTunes Device Support Update and had no problems syncing apps on an iPad Air 2 and iPhone SE using iTunes 12.6.5.3. I then successfully updated both devices from iOS 12.2 to 12.3 using iTunes.

I have no reason to perform a Restore at the moment, but so far, so good.

Just for fun, I updated an identical iPhone SE to 12.3 over WiFi. It completed about two minutes faster than doing it through iTunes. :) your milage may vary.

I haven't bought any new music for some time, having an extensive personal collection. The last couple days I have been poking around in the Apple store trying to buy a classical album for my collection, but all I find are pitches to try Apple Music free for 3 months. I see some selections with prices listed, but when I search for specific albums, they display without any price and the implication all I can do is stream them via Apple Music.

I suppose I could accumulate a set of albums I want, subscribe free to Apple Music long enough to download them, and then cancel Apple Music, but I would prefer the old purchase model. Does it still exist and how do I get to it?

I know, Apple Music is really frustrating when you don't want it, as Apple always put it in your face, all the time! The old model does still exist - you could use the iTunes Link Maker to find and buy music:

Search for the music you want (if it does not show up, then it is either not available in your country or it is only available for streaming via an Apple Music subscription - you can change the Store Country and/or Media Type to "Apple Music" to check this theory)

When you find the music you want with Media Type set to "Music", click on the "Album" you want

Click on the "Direct Link" at the bottom (this will open a new window/tab in your browser of choice to that album page) and may open the iTunes application automatically

Click the blue "View in iTunes" button at the top if the iTunes application doesn't open automatically

The iTunes application should show the iTunes Store with the "Buy" button (with price) below the album artwork on the left

The last couple days I have been poking around in the Apple store trying to buy a classical album for my collection, but all I find are pitches to try Apple Music free for 3 months. I see some selections with prices listed, but when I search for specific albums, they display without any price and the implication all I can do is stream them via Apple Music.